Billy Madison

Billy Madison is a 1995 farce starring Adam Sandler as the title role. Also features Brad Whitford, Josh Mostel, Bridgette Wilson, Chris Farley, and Darren McGavin.

Spoiler warning: Plot or ending details follow.

Madison is a grown up son of a hotel tycoon who spends most of his time being drunk around the house, chasing an imaginary penguin, and putting flaming bags of dog feces on his neighbor's lawn. When his father (McGavin) announces his retirement, he chooses his vice president (Whitford), not Billy. Billy makes a bet that he is smart enough to run the company. If he goes back to school starting from first grade to twelveth, and graduates each grade in two weeks, he gains control of Madison Hotels.